Formation of oligopeptides in high yield under simple programmable conditions
Formation of oligopeptides in high yield under simple programmable conditions
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DOI：
10.1038/ncomms9385
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发表时间：
2015-10-01
影响因子：
16.6
通讯作者：
Cronin, Leroy
中科院分区：
文献类型：
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作者：
Rodriguez-Garcia, Marc;Surman, Andrew J.;Cronin, Leroy
已经开发了许多用于形成肽键的高产率反应，但这些反应都很复杂，需要活化的氨基酸前体和多相载体。在这里，我们展示了可编程一锅脱水-水合缩合形成寡肽链的氨基酸，产率约为50%。开发了一个数字递归反应器系统来研究这一过程，通过控制温度、循环次数、循环持续时间、初始单体浓度和初始pH等参数来执行这些反应。长达20个氨基酸的甘氨酸低聚肽的形成具有很高的单体到低聚物的转化率，并且这些产物中的大多数由三个或更多氨基酸残基组成。在确定了甘氨酸低聚肽的形成后，我们展示了甘氨酸与其他八种氨基酸(丙氨酸、天冬氨酸、谷氨酸、组氨酸、赖氨酸、Pro、苏氨酸和Val)的共缩合，结合了一系列侧链功能。
Many high-yielding reactions for forming peptide bonds have been developed but these are complex, requiring activated amino-acid precursors and heterogeneous supports. Herein we demonstrate the programmable one-pot dehydration-hydration condensation of amino acids forming oligopeptide chains in around 50% yield. A digital recursive reactor system was developed to investigate this process, performing these reactions with control over parameters such as temperature, number of cycles, cycle duration, initial monomer concentration and initial pH. Glycine oligopeptides up to 20 amino acids long were formed with very high monomer-to-oligomer conversion, and the majority of these products comprised three amino acid residues or more. Having established the formation of glycine homo-oligopeptides, we then demonstrated the co-condensation of glycine with eight other amino acids (Ala, Asp, Glu, His, Lys, Pro, Thr and Val), incorporating a range of side-chain functionality.